CA2704981A1 - Aldh-2 inhibitors in the treatment of psychiatric disorders - Google Patents
Aldh-2 inhibitors in the treatment of psychiatric disorders Download PDFInfo
- Publication number
- CA2704981A1 CA2704981A1 CA2704981A CA2704981A CA2704981A1 CA 2704981 A1 CA2704981 A1 CA 2704981A1 CA 2704981 A CA2704981 A CA 2704981A CA 2704981 A CA2704981 A CA 2704981A CA 2704981 A1 CA2704981 A1 CA 2704981A1
- Authority
- CA
- Canada
- Prior art keywords
- chromen
- hydroxyphenyl
- phenyl
- methoxy
- trifluoromethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000003112 inhibitor Substances 0.000 title claims abstract description 25
- 208000020016 psychiatric disease Diseases 0.000 title claims abstract description 15
- 238000011282 treatment Methods 0.000 title description 20
- 208000019906 panic disease Diseases 0.000 claims abstract description 20
- 206010041250 Social phobia Diseases 0.000 claims abstract description 9
- 208000019116 sleep disease Diseases 0.000 claims abstract description 9
- 241000124008 Mammalia Species 0.000 claims abstract description 6
- 208000037870 generalized anxiety Diseases 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 264
- -1 heteroaryl amide Chemical class 0.000 claims description 118
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 101
- 125000000217 alkyl group Chemical group 0.000 claims description 93
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 72
- 238000000034 method Methods 0.000 claims description 72
- 125000001072 heteroaryl group Chemical group 0.000 claims description 70
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 68
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 claims description 58
- 239000001257 hydrogen Substances 0.000 claims description 58
- 229910052739 hydrogen Inorganic materials 0.000 claims description 58
- 125000003118 aryl group Chemical group 0.000 claims description 54
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 52
- 125000001424 substituent group Chemical group 0.000 claims description 51
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 48
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- 125000003545 alkoxy group Chemical group 0.000 claims description 37
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 150000002367 halogens Chemical group 0.000 claims description 34
- 229910052760 oxygen Inorganic materials 0.000 claims description 34
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 33
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 33
- 239000001301 oxygen Substances 0.000 claims description 33
- 208000019901 Anxiety disease Diseases 0.000 claims description 28
- 125000002947 alkylene group Chemical group 0.000 claims description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 125000003342 alkenyl group Chemical group 0.000 claims description 24
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 230000036506 anxiety Effects 0.000 claims description 22
- 125000000304 alkynyl group Chemical group 0.000 claims description 20
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
- 239000005711 Benzoic acid Substances 0.000 claims description 8
- 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 claims description 8
- ZHXTWWCDMUWMDI-UHFFFAOYSA-N dihydroxyboron Chemical compound O[B]O ZHXTWWCDMUWMDI-UHFFFAOYSA-N 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- YYOOFJZTRCPVFD-UHFFFAOYSA-N 3-[[3-[4-(methanesulfonamido)phenyl]-4-oxochromen-7-yl]oxymethyl]benzoic acid Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(O)=O)=CC=C2C1=O YYOOFJZTRCPVFD-UHFFFAOYSA-N 0.000 claims description 7
- 125000004193 piperazinyl group Chemical group 0.000 claims description 7
- 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 claims description 6
- XINYOLXTIGKVRM-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-oxo-2-[2-(trifluoromethyl)phenyl]ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC(=O)C=3C(=CC=CC=3)C(F)(F)F)=CC=C2C1=O XINYOLXTIGKVRM-UHFFFAOYSA-N 0.000 claims description 6
- YEVVMGQTIHYLHJ-CYBMUJFWSA-N 7-[(1r)-1-[3-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound O([C@H](C)C=1ON=C(N=1)C=1C=C(C=C(F)C=1)C(F)(F)F)C(C=1)=CC=C(C2=O)C=1OC=C2C1=CC=C(O)C=C1 YEVVMGQTIHYLHJ-CYBMUJFWSA-N 0.000 claims description 6
- FYMBTIMJLANAIU-UHFFFAOYSA-N 7-[[2-[3-fluoro-5-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(OC=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O FYMBTIMJLANAIU-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Chemical group N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- BISVYANBIFBJIA-UHFFFAOYSA-N 2-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy-n-[3-(trifluoromethyl)phenyl]acetamide Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC(=O)NC=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O BISVYANBIFBJIA-UHFFFAOYSA-N 0.000 claims description 5
- SKVYHLULOMUGKX-UHFFFAOYSA-N 2-fluoro-5-[7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]benzonitrile Chemical compound FC(F)(F)C1=CC(F)=CC(C=2ON=C(COC=3C=C4C(C(C(C=5C=C(C(F)=CC=5)C#N)=CO4)=O)=CC=3)N=2)=C1 SKVYHLULOMUGKX-UHFFFAOYSA-N 0.000 claims description 5
- UIUCEBUXYPDPAJ-UHFFFAOYSA-N 3-(3-acetylphenyl)-7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound CC(=O)C1=CC=CC(C=2C(C3=CC=C(OCC=4N=C(ON=4)C=4C=C(C=C(F)C=4)C(F)(F)F)C=C3OC=2)=O)=C1 UIUCEBUXYPDPAJ-UHFFFAOYSA-N 0.000 claims description 5
- GFHOVQHRHREPPZ-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-(3-phenylpropoxy)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCCC=3C=CC=CC=3)=CC=C2C1=O GFHOVQHRHREPPZ-UHFFFAOYSA-N 0.000 claims description 5
- FXSYGQPEYZJTHI-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-(5-pyridin-3-yl-1,3,4-oxadiazol-2-yl)ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3OC(=NN=3)C=3C=NC=CC=3)=CC=C2C1=O FXSYGQPEYZJTHI-UHFFFAOYSA-N 0.000 claims description 5
- GUZLXSMJFYJQFJ-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-(5-pyridin-4-yl-1,2,4-oxadiazol-3-yl)ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3N=C(ON=3)C=3C=CN=CC=3)=CC=C2C1=O GUZLXSMJFYJQFJ-UHFFFAOYSA-N 0.000 claims description 5
- MGBNIYZXARWXHW-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3ON=C(N=3)C=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O MGBNIYZXARWXHW-UHFFFAOYSA-N 0.000 claims description 5
- JGOMKMRNUIOXIC-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-[3-(trifluoromethyl)phenyl]-1,2-oxazol-3-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC3=NOC(=C3)C=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O JGOMKMRNUIOXIC-UHFFFAOYSA-N 0.000 claims description 5
- NXRZHVXCUDNZGL-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[6-(1h-pyrazol-5-yl)pyridin-3-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=NC(=CC=3)C3=NNC=C3)=CC=C2C1=O NXRZHVXCUDNZGL-UHFFFAOYSA-N 0.000 claims description 5
- XAYXXBMMIHLDQI-UHFFFAOYSA-N 3-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)=C1 XAYXXBMMIHLDQI-UHFFFAOYSA-N 0.000 claims description 5
- JUCBBVFEJTVYFD-UHFFFAOYSA-N 4-[7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O JUCBBVFEJTVYFD-UHFFFAOYSA-N 0.000 claims description 5
- HSTCXSZUDZOKRP-UHFFFAOYSA-N 7-[2-(3-fluorophenyl)-2-oxoethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC(=O)C=3C=C(F)C=CC=3)=CC=C2C1=O HSTCXSZUDZOKRP-UHFFFAOYSA-N 0.000 claims description 5
- RKGISUHWZBBCKR-UHFFFAOYSA-N 7-[2-[3-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3ON=C(N=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O RKGISUHWZBBCKR-UHFFFAOYSA-N 0.000 claims description 5
- 235000010233 benzoic acid Nutrition 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- PNNQLSVOFZVQDZ-HNNXBMFYSA-N n-[(1s)-1-(4-fluorophenyl)ethyl]-2-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyacetamide Chemical compound N([C@@H](C)C=1C=CC(F)=CC=1)C(=O)COC(C=1)=CC=C(C2=O)C=1OC=C2C1=CC=C(O)C=C1 PNNQLSVOFZVQDZ-HNNXBMFYSA-N 0.000 claims description 5
- PMXLLFNDTDRGFI-UHFFFAOYSA-N n-[4-[7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O PMXLLFNDTDRGFI-UHFFFAOYSA-N 0.000 claims description 5
- WGSXKYXKAARAKD-UHFFFAOYSA-N 1-fluoro-3-isocyanato-5-(trifluoromethyl)benzene Chemical group FC1=CC(N=C=O)=CC(C(F)(F)F)=C1 WGSXKYXKAARAKD-UHFFFAOYSA-N 0.000 claims description 4
- QXODMLJSSSYMLK-UHFFFAOYSA-N 2-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy-n-[2-(trifluoromethyl)phenyl]acetamide Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC(=O)NC=3C(=CC=CC=3)C(F)(F)F)=CC=C2C1=O QXODMLJSSSYMLK-UHFFFAOYSA-N 0.000 claims description 4
- JUEBRUJMZIBZFF-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O JUEBRUJMZIBZFF-UHFFFAOYSA-N 0.000 claims description 4
- HEOQQDCLAMIWDE-UHFFFAOYSA-N 3-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]benzonitrile Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C#N)=CC=C2C1=O HEOQQDCLAMIWDE-UHFFFAOYSA-N 0.000 claims description 4
- WCTAYNZYWWPMBP-UHFFFAOYSA-N 3-[[3-[4-(methanesulfonamido)phenyl]-4-oxochromen-7-yl]oxymethyl]benzamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(N)=O)=CC=C2C1=O WCTAYNZYWWPMBP-UHFFFAOYSA-N 0.000 claims description 4
- FAHBJKISWFYSTG-UHFFFAOYSA-N 7-[[5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=CC(F)=CC=3)=CC=C2C1=O FAHBJKISWFYSTG-UHFFFAOYSA-N 0.000 claims description 4
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical group N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical group C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 4
- 101100240527 Caenorhabditis elegans nhr-22 gene Proteins 0.000 claims description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 4
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical group C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- PNNQLSVOFZVQDZ-OAHLLOKOSA-N n-[(1r)-1-(4-fluorophenyl)ethyl]-2-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyacetamide Chemical compound N([C@H](C)C=1C=CC(F)=CC=1)C(=O)COC(C=1)=CC=C(C2=O)C=1OC=C2C1=CC=C(O)C=C1 PNNQLSVOFZVQDZ-OAHLLOKOSA-N 0.000 claims description 4
- IXNLDMMIZOOUOV-UHFFFAOYSA-N n-[4-[7-[(3-cyanophenyl)methoxy]-4-oxochromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C#N)=CC=C2C1=O IXNLDMMIZOOUOV-UHFFFAOYSA-N 0.000 claims description 4
- FIFFBIMRAZGZIN-UHFFFAOYSA-N n-[4-[7-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methoxy]-4-oxochromen-3-yl]phenyl]methanesulfonamide Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1COC(C=1)=CC=C(C2=O)C=1OC=C2C1=CC=C(NS(C)(=O)=O)C=C1 FIFFBIMRAZGZIN-UHFFFAOYSA-N 0.000 claims description 4
- QXYPVJQYTBVSBE-UHFFFAOYSA-N n-[4-[7-[[5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=CC(F)=CC=3)=CC=C2C1=O QXYPVJQYTBVSBE-UHFFFAOYSA-N 0.000 claims description 4
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 claims description 4
- YARRGUWVCVLKCS-UHFFFAOYSA-N 2-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]-1,3-oxazole-4-carboxylic acid Chemical compound OC(=O)C1=COC(COC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)=N1 YARRGUWVCVLKCS-UHFFFAOYSA-N 0.000 claims description 3
- QZQVAPKTAUQPCF-UHFFFAOYSA-N 2-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]-N-methyl-1,3-oxazole-4-carboxamide Chemical compound CNC(=O)C1=COC(COC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)=N1 QZQVAPKTAUQPCF-UHFFFAOYSA-N 0.000 claims description 3
- OESBYEICGXYNBT-UHFFFAOYSA-N 3-(4-aminophenyl)-7-[[5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound C1=CC(N)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O OESBYEICGXYNBT-UHFFFAOYSA-N 0.000 claims description 3
- MLHOACBDJNPKJC-UHFFFAOYSA-N 3-(4-aminophenyl)-7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound C1=CC(N)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O MLHOACBDJNPKJC-UHFFFAOYSA-N 0.000 claims description 3
- ZJWNWERIHPKYCW-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-(2-phenylethoxy)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3C=CC=CC=3)=CC=C2C1=O ZJWNWERIHPKYCW-UHFFFAOYSA-N 0.000 claims description 3
- CTTKSJXFCLZWEY-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-(2-piperazin-1-ylethoxy)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCNCC3)=CC=C2C1=O CTTKSJXFCLZWEY-UHFFFAOYSA-N 0.000 claims description 3
- GABUIDRLSZLRFS-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-(pyridin-2-ylmethoxy)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=CC=CC=3)=CC=C2C1=O GABUIDRLSZLRFS-UHFFFAOYSA-N 0.000 claims description 3
- LYOPHGBGGFBIAP-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-(pyridin-4-ylmethoxy)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=CN=CC=3)=CC=C2C1=O LYOPHGBGGFBIAP-UHFFFAOYSA-N 0.000 claims description 3
- SGWYZMJMBDTNPE-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[(3-phenyl-1,2,4-oxadiazol-5-yl)methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3ON=C(N=3)C=3C=CC=CC=3)=CC=C2C1=O SGWYZMJMBDTNPE-UHFFFAOYSA-N 0.000 claims description 3
- GQHHGMIEWPYQLZ-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[(3-pyridin-3-yl-1,2,4-oxadiazol-5-yl)methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3ON=C(N=3)C=3C=NC=CC=3)=CC=C2C1=O GQHHGMIEWPYQLZ-UHFFFAOYSA-N 0.000 claims description 3
- FFXQJURUOMILQH-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[(5-phenyl-1,2,4-oxadiazol-3-yl)methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=CC=CC=3)=CC=C2C1=O FFXQJURUOMILQH-UHFFFAOYSA-N 0.000 claims description 3
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- TZRVABAXGZCOOH-UHFFFAOYSA-N 7-[[5-[2,5-bis(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C(=CC=C(C=3)C(F)(F)F)C(F)(F)F)=CC=C2C1=O TZRVABAXGZCOOH-UHFFFAOYSA-N 0.000 claims description 3
- NPGQORNIHHVBJO-UHFFFAOYSA-N 7-[[5-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=C(C=3)C(F)(F)F)C(F)(F)F)=CC=C2C1=O NPGQORNIHHVBJO-UHFFFAOYSA-N 0.000 claims description 3
- CDZYCQRKIXMTJK-UHFFFAOYSA-N 7-[[5-[3,5-bis(trifluoromethyl)phenyl]-1,2-oxazol-3-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC3=NOC(=C3)C=3C=C(C=C(C=3)C(F)(F)F)C(F)(F)F)=CC=C2C1=O CDZYCQRKIXMTJK-UHFFFAOYSA-N 0.000 claims description 3
- GVOQTGJRDTXIMR-UHFFFAOYSA-N 7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O GVOQTGJRDTXIMR-UHFFFAOYSA-N 0.000 claims description 3
- CLFPJUWQTLWOEP-UHFFFAOYSA-N 7-[[5-[4-fluoro-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C(F)=CC=3)C(F)(F)F)=CC=C2C1=O CLFPJUWQTLWOEP-UHFFFAOYSA-N 0.000 claims description 3
- 229910007161 Si(CH3)3 Inorganic materials 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- AAWXSHHENRRQRE-UHFFFAOYSA-N ethyl 1-[2-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyethyl]pyrazole-4-carboxylate Chemical compound C1=C(C(=O)OCC)C=NN1CCOC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 AAWXSHHENRRQRE-UHFFFAOYSA-N 0.000 claims description 3
- GKIIYMRXUSLEFZ-UHFFFAOYSA-N ethyl 4-[7-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methoxy]-4-oxochromen-3-yl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1C1=COC2=CC(OCC3=C(N=C(S3)C=3C=CC(=CC=3)C(F)(F)F)C)=CC=C2C1=O GKIIYMRXUSLEFZ-UHFFFAOYSA-N 0.000 claims description 3
- IVLDGUKVQHCQCA-UHFFFAOYSA-N methyl 2-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]-1,3-oxazole-4-carboxylate Chemical compound COC(=O)C1=COC(COC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)=N1 IVLDGUKVQHCQCA-UHFFFAOYSA-N 0.000 claims description 3
- FKSRMBLWEXMUQH-UHFFFAOYSA-N methyl 3-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]benzoate Chemical compound COC(=O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)=C1 FKSRMBLWEXMUQH-UHFFFAOYSA-N 0.000 claims description 3
- XCGPDNAYSXIGBN-UHFFFAOYSA-N methyl 3-[[3-[4-(hydroxymethyl)phenyl]-4-oxochromen-7-yl]oxymethyl]benzoate Chemical compound COC(=O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=CC(CO)=CC=4)=CO3)=O)=CC=2)=C1 XCGPDNAYSXIGBN-UHFFFAOYSA-N 0.000 claims description 3
- GGWNBYMSLMPZCF-UHFFFAOYSA-N methyl 3-[[3-[4-(methanesulfonamido)phenyl]-4-oxochromen-7-yl]oxymethyl]benzoate Chemical compound COC(=O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=CC(NS(C)(=O)=O)=CC=4)=CO3)=O)=CC=2)=C1 GGWNBYMSLMPZCF-UHFFFAOYSA-N 0.000 claims description 3
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- IEHKIQDJTOPPTN-UHFFFAOYSA-N n-(3-fluorophenyl)-2-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyacetamide Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC(=O)NC=3C=C(F)C=CC=3)=CC=C2C1=O IEHKIQDJTOPPTN-UHFFFAOYSA-N 0.000 claims description 3
- SZCZFEMWSJXEAC-UHFFFAOYSA-N n-(3-fluorophenyl)-4-[2-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyethyl]piperazine-1-carboxamide Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCN(CC3)C(=O)NC=3C=C(F)C=CC=3)=CC=C2C1=O SZCZFEMWSJXEAC-UHFFFAOYSA-N 0.000 claims description 3
- FNYQPJGJSIQOQK-UHFFFAOYSA-N n-[4-[4-oxo-7-[(2-phenyl-1,3-oxazol-4-yl)methoxy]chromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3N=C(OC=3)C=3C=CC=CC=3)=CC=C2C1=O FNYQPJGJSIQOQK-UHFFFAOYSA-N 0.000 claims description 3
- ARHPCVRPEMHVFN-UHFFFAOYSA-N n-[4-[4-oxo-7-[[5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O ARHPCVRPEMHVFN-UHFFFAOYSA-N 0.000 claims description 3
- SCXVTUJUIPDVJB-UHFFFAOYSA-N n-[4-[7-[[5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl]methoxy]-4-oxochromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3OC(=NN=3)C=3C=CC(F)=CC=3)=CC=C2C1=O SCXVTUJUIPDVJB-UHFFFAOYSA-N 0.000 claims description 3
- NJYMIOGEDYKFQY-UHFFFAOYSA-N n-[4-[7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]phenyl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=C(C=2C(C3=CC=C(OCC=4N=C(ON=4)C=4C=C(C=C(F)C=4)C(F)(F)F)C=C3OC=2)=O)C=C1 NJYMIOGEDYKFQY-UHFFFAOYSA-N 0.000 claims description 3
- YLOBJVZLCAELSS-UHFFFAOYSA-N prop-2-enyl 3-[3-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]-1,2,4-oxadiazol-5-yl]benzoate Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=CC=3)C(=O)OCC=C)=CC=C2C1=O YLOBJVZLCAELSS-UHFFFAOYSA-N 0.000 claims description 3
- FJZJXFQFHMJTSI-UHFFFAOYSA-N prop-2-enyl 3-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]benzoate Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(=O)OCC=C)=CC=C2C1=O FJZJXFQFHMJTSI-UHFFFAOYSA-N 0.000 claims description 3
- 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 claims description 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical group C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 2
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- VLRSADZEDXVUPG-UHFFFAOYSA-N 2-naphthalen-1-ylpyridine Chemical group N1=CC=CC=C1C1=CC=CC2=CC=CC=C12 VLRSADZEDXVUPG-UHFFFAOYSA-N 0.000 claims description 2
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical group C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 2
- BCHLRGSTGMUSFO-UHFFFAOYSA-N 3-[[3-(4-aminophenyl)-4-oxochromen-7-yl]oxymethyl]benzoic acid Chemical compound C1=CC(N)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(O)=O)=CC=C2C1=O BCHLRGSTGMUSFO-UHFFFAOYSA-N 0.000 claims description 2
- VFKSORDIMAUFFL-UHFFFAOYSA-N 4-(oxathian-3-yl)morpholine Chemical group O1SC(CCC1)N1CCOCC1 VFKSORDIMAUFFL-UHFFFAOYSA-N 0.000 claims description 2
- GDRVFDDBLLKWRI-UHFFFAOYSA-N 4H-quinolizine Chemical group C1=CC=CN2CC=CC=C21 GDRVFDDBLLKWRI-UHFFFAOYSA-N 0.000 claims description 2
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- YYGCAYSDPMCHAO-UHFFFAOYSA-N 7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-3-(4-methylsulfonylphenyl)chromen-4-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O YYGCAYSDPMCHAO-UHFFFAOYSA-N 0.000 claims description 2
- RKVAGAXJZJFEDQ-UHFFFAOYSA-N 7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-3-[4-(hydroxymethyl)phenyl]chromen-4-one Chemical compound C1=CC(CO)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O RKVAGAXJZJFEDQ-UHFFFAOYSA-N 0.000 claims description 2
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 2
- AMJINJSTVXQTMD-UHFFFAOYSA-N [4-[7-[[2-[3-fluoro-5-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]methoxy]-4-oxochromen-3-yl]phenyl] dihydrogen phosphate Chemical compound C1=CC(OP(O)(=O)O)=CC=C1C1=COC2=CC(OCC=3N=C(OC=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O AMJINJSTVXQTMD-UHFFFAOYSA-N 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical group N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Chemical group CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Chemical group C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical group C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 claims description 2
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
- CFXFFAFGWRNMJV-UHFFFAOYSA-N methyl 4-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1COC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 CFXFFAFGWRNMJV-UHFFFAOYSA-N 0.000 claims description 2
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- 229950000688 phenothiazine Drugs 0.000 claims description 2
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical group C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- QVZCPNUNJCOGGA-UHFFFAOYSA-N propan-2-yl 3-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]benzoate Chemical compound CC(C)OC(=O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)=C1 QVZCPNUNJCOGGA-UHFFFAOYSA-N 0.000 claims description 2
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical group N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 claims description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical group N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 2
- 125000005505 thiomorpholino group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 6
- 125000001475 halogen functional group Chemical group 0.000 claims 5
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 claims 1
- DKYBVKMIZODYKL-UHFFFAOYSA-N 1,3-diazinane Chemical compound C1CNCNC1 DKYBVKMIZODYKL-UHFFFAOYSA-N 0.000 claims 1
- QYQCFHLVHVSJTA-UHFFFAOYSA-N 2-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]benzonitrile Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C(=CC=CC=3)C#N)=CC=C2C1=O QYQCFHLVHVSJTA-UHFFFAOYSA-N 0.000 claims 1
- NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 claims 1
- DKTXNAYSCCZCGS-UHFFFAOYSA-N 2-trimethylsilylethyl 3-[[3-(3-cyanophenyl)-4-oxochromen-7-yl]oxymethyl]benzoate Chemical compound C[Si](C)(C)CCOC(=O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=C(C=CC=4)C#N)=CO3)=O)=CC=2)=C1 DKTXNAYSCCZCGS-UHFFFAOYSA-N 0.000 claims 1
- LNLIHPSCCYLOHF-UHFFFAOYSA-N 2-trimethylsilylethyl 3-[[3-(4-carbamoylphenyl)-4-oxochromen-7-yl]oxymethyl]benzoate Chemical compound C[Si](C)(C)CCOC(=O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=CC(=CC=4)C(N)=O)=CO3)=O)=CC=2)=C1 LNLIHPSCCYLOHF-UHFFFAOYSA-N 0.000 claims 1
- CNFOIZLFPBENBM-UHFFFAOYSA-N 3-(3-fluorophenyl)-7-[[5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound FC1=CC=CC(C=2C(C3=CC=C(OCC=4N=C(ON=4)C=4C=C(C=CC=4)C(F)(F)F)C=C3OC=2)=O)=C1 CNFOIZLFPBENBM-UHFFFAOYSA-N 0.000 claims 1
- XUJUWOOYHUYKRF-UHFFFAOYSA-N 3-(4-aminophenyl)-7-[[3-(trifluoromethoxy)phenyl]methoxy]chromen-4-one Chemical compound C1=CC(N)=CC=C1C1=COC2=CC(OCC=3C=C(OC(F)(F)F)C=CC=3)=CC=C2C1=O XUJUWOOYHUYKRF-UHFFFAOYSA-N 0.000 claims 1
- QVCQIPUPLJTJKR-UHFFFAOYSA-N 3-(4-aminophenyl)-7-[[3-(trifluoromethyl)phenyl]methoxy]chromen-4-one Chemical compound C1=CC(N)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O QVCQIPUPLJTJKR-UHFFFAOYSA-N 0.000 claims 1
- USHIWOJJGWWHKC-UHFFFAOYSA-N 3-(4-fluorophenyl)-7-[[5-(2-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound COC1=CC=CC=C1C1=NC(COC=2C=C3C(C(C(C=4C=CC(F)=CC=4)=CO3)=O)=CC=2)=NO1 USHIWOJJGWWHKC-UHFFFAOYSA-N 0.000 claims 1
- UNYJSYKAFBRDSF-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-6-[[3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C(C(C1=C2)=O)=COC1=CC=C2OCC1=NC(C=2C=C(C=CC=2)C(F)(F)F)=NO1 UNYJSYKAFBRDSF-UHFFFAOYSA-N 0.000 claims 1
- IGLFEFCJHYKGNJ-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-6-[[5-[4-methoxy-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-2-(trifluoromethyl)chromen-4-one Chemical compound C1=C(C(F)(F)F)C(OC)=CC=C1C1=NC(COC=2C=C3C(=O)C(C=4C=CC(O)=CC=4)=C(OC3=CC=2)C(F)(F)F)=NO1 IGLFEFCJHYKGNJ-UHFFFAOYSA-N 0.000 claims 1
- BTNOQJRRJASMJW-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-(pyridin-3-ylmethoxy)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=NC=CC=3)=CC=C2C1=O BTNOQJRRJASMJW-UHFFFAOYSA-N 0.000 claims 1
- MYLUNEORTANDOK-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[(2-phenyl-1,3-oxazol-4-yl)methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3N=C(OC=3)C=3C=CC=CC=3)=CC=C2C1=O MYLUNEORTANDOK-UHFFFAOYSA-N 0.000 claims 1
- YBSGKKITPLSUPH-FQEVSTJZSA-N 3-(4-hydroxyphenyl)-7-[(2s)-2-hydroxy-3-[[3-(trifluoromethyl)phenyl]methylamino]propoxy]chromen-4-one Chemical compound C([C@H](O)COC=1C=C2C(C(C(C=3C=CC(O)=CC=3)=CO2)=O)=CC=1)NCC1=CC=CC(C(F)(F)F)=C1 YBSGKKITPLSUPH-FQEVSTJZSA-N 0.000 claims 1
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- QPOMIYFFWNHPDD-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[(5-phenyl-1,2-oxazol-3-yl)methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC3=NOC(=C3)C=3C=CC=CC=3)=CC=C2C1=O QPOMIYFFWNHPDD-UHFFFAOYSA-N 0.000 claims 1
- FPUFUYUDPHGFEH-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-(5-pyridin-4-yl-1,3,4-oxadiazol-2-yl)ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3OC(=NN=3)C=3C=CN=CC=3)=CC=C2C1=O FPUFUYUDPHGFEH-UHFFFAOYSA-N 0.000 claims 1
- XNRHIWZNASULGF-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethoxy]chromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCOC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)CC1 XNRHIWZNASULGF-UHFFFAOYSA-N 0.000 claims 1
- VOZPBFARGKFKDU-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[4-(2-methylphenyl)piperazin-1-yl]ethoxy]chromen-4-one Chemical compound CC1=CC=CC=C1N1CCN(CCOC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)CC1 VOZPBFARGKFKDU-UHFFFAOYSA-N 0.000 claims 1
- GKDBURVCBFZSCD-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[4-(3-methoxyphenyl)piperazin-1-yl]ethoxy]chromen-4-one Chemical compound COC1=CC=CC(N2CCN(CCOC=3C=C4C(C(C(C=5C=CC(O)=CC=5)=CO4)=O)=CC=3)CC2)=C1 GKDBURVCBFZSCD-UHFFFAOYSA-N 0.000 claims 1
- MVWFUJHZXMTRHS-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[4-(3-methylphenyl)piperazin-1-yl]ethoxy]chromen-4-one Chemical compound CC1=CC=CC(N2CCN(CCOC=3C=C4C(C(C(C=5C=CC(O)=CC=5)=CO4)=O)=CC=3)CC2)=C1 MVWFUJHZXMTRHS-UHFFFAOYSA-N 0.000 claims 1
- STVSMLYUQNAJLH-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[4-(4-methylphenyl)piperazin-1-yl]ethoxy]chromen-4-one Chemical compound C1=CC(C)=CC=C1N1CCN(CCOC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)CC1 STVSMLYUQNAJLH-UHFFFAOYSA-N 0.000 claims 1
- KPWVMSRCNSRFBT-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[4-[2-(trifluoromethyl)phenyl]piperazin-1-yl]ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCN(CC3)C=3C(=CC=CC=3)C(F)(F)F)=CC=C2C1=O KPWVMSRCNSRFBT-UHFFFAOYSA-N 0.000 claims 1
- HABMRRNWPZNAHB-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCN(CC3)C=3C=CC(=CC=3)C(F)(F)F)=CC=C2C1=O HABMRRNWPZNAHB-UHFFFAOYSA-N 0.000 claims 1
- QIMFQFMJFVNZFR-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[2-oxo-2-[4-(trifluoromethyl)phenyl]ethoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC(=O)C=3C=CC(=CC=3)C(F)(F)F)=CC=C2C1=O QIMFQFMJFVNZFR-UHFFFAOYSA-N 0.000 claims 1
- ZPUVRABODOBSAH-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[3-(trifluoromethoxy)phenyl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=C(OC(F)(F)F)C=CC=3)=CC=C2C1=O ZPUVRABODOBSAH-UHFFFAOYSA-N 0.000 claims 1
- XZWFEHFXGWFMKS-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[3-[3-(trifluoromethyl)phenyl]-1,2-oxazol-5-yl]methoxy]chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3ON=C(C=3)C=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O XZWFEHFXGWFMKS-UHFFFAOYSA-N 0.000 claims 1
- VFUZTXQSDASORI-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-(2-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methoxy]chromen-4-one Chemical compound COC1=CC=CC=C1C(O1)=NN=C1COC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 VFUZTXQSDASORI-UHFFFAOYSA-N 0.000 claims 1
- RMXOJOGIANOTSJ-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-(2-methylphenyl)-1,3,4-oxadiazol-2-yl]methoxy]chromen-4-one Chemical compound CC1=CC=CC=C1C(O1)=NN=C1COC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 RMXOJOGIANOTSJ-UHFFFAOYSA-N 0.000 claims 1
- FUCKCJMQAGFLIF-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-(3-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methoxy]chromen-4-one Chemical compound COC1=CC=CC(C=2OC(COC=3C=C4C(C(C(C=5C=CC(O)=CC=5)=CO4)=O)=CC=3)=NN=2)=C1 FUCKCJMQAGFLIF-UHFFFAOYSA-N 0.000 claims 1
- SLDDEMWKXMOGSY-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-(3-methylphenyl)-1,3,4-oxadiazol-2-yl]methoxy]chromen-4-one Chemical compound CC1=CC=CC(C=2OC(COC=3C=C4C(C(C(C=5C=CC(O)=CC=5)=CO4)=O)=CC=3)=NN=2)=C1 SLDDEMWKXMOGSY-UHFFFAOYSA-N 0.000 claims 1
- SCIHYFZNPVIOOQ-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-(4-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound C1=CC(OC)=CC=C1C1=NC(COC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)=NO1 SCIHYFZNPVIOOQ-UHFFFAOYSA-N 0.000 claims 1
- VQAIBBQEMDSXGR-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methoxy]chromen-4-one Chemical compound C1=CC(OC)=CC=C1C(O1)=NN=C1COC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 VQAIBBQEMDSXGR-UHFFFAOYSA-N 0.000 claims 1
- ZRCYZRQZQQCIAK-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]methoxy]chromen-4-one Chemical compound C1=CC(C)=CC=C1C(O1)=NN=C1COC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 ZRCYZRQZQQCIAK-UHFFFAOYSA-N 0.000 claims 1
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- KRTVXOPDCMVMGC-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-7-[[5-[4-methoxy-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound C1=C(C(F)(F)F)C(OC)=CC=C1C1=NC(COC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)=NO1 KRTVXOPDCMVMGC-UHFFFAOYSA-N 0.000 claims 1
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- PKGVXZWMYVCZNT-UHFFFAOYSA-N 3-(4-methoxyphenyl)-7-[[5-(2-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound C1=CC(OC)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C(=CC=CC=3)OC)=CC=C2C1=O PKGVXZWMYVCZNT-UHFFFAOYSA-N 0.000 claims 1
- RGQMOEXUFWMRLU-UHFFFAOYSA-N 3-(4-methylphenyl)-7-[[5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-4-one Chemical compound C1=CC(C)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O RGQMOEXUFWMRLU-UHFFFAOYSA-N 0.000 claims 1
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- KFLSGMZNSZFNAJ-UHFFFAOYSA-N 4-[4-oxo-7-[[5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]chromen-3-yl]benzonitrile Chemical compound FC(F)(F)C1=CC=CC(C=2ON=C(COC=3C=C4C(C(C(C=5C=CC(=CC=5)C#N)=CO4)=O)=CC=3)N=2)=C1 KFLSGMZNSZFNAJ-UHFFFAOYSA-N 0.000 claims 1
- VFRTZXWTORJKEU-UHFFFAOYSA-N 4-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]benzonitrile Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=CC(=CC=3)C#N)=CC=C2C1=O VFRTZXWTORJKEU-UHFFFAOYSA-N 0.000 claims 1
- CXIIQPMREFANFO-UHFFFAOYSA-N 6-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-3-(4-hydroxyphenyl)-2-(trifluoromethyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C(C(C1=C2)=O)=C(C(F)(F)F)OC1=CC=C2OCC1=NOC(C=2C=C(C=C(F)C=2)C(F)(F)F)=N1 CXIIQPMREFANFO-UHFFFAOYSA-N 0.000 claims 1
- RPQZKJITPGRCKF-FQEVSTJZSA-N 7-[(2s)-2-hydroxy-3-[[3-(trifluoromethyl)phenyl]methylamino]propoxy]-3-(4-methoxyphenyl)chromen-4-one Chemical compound C1=CC(OC)=CC=C1C1=COC2=CC(OC[C@@H](O)CNCC=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O RPQZKJITPGRCKF-FQEVSTJZSA-N 0.000 claims 1
- BHESGBIBNPDUJW-FQEVSTJZSA-N 7-[(2s)-3-[(3,5-difluorophenyl)methylamino]-2-hydroxypropoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C([C@H](O)COC=1C=C2C(C(C(C=3C=CC(O)=CC=3)=CO2)=O)=CC=1)NCC1=CC(F)=CC(F)=C1 BHESGBIBNPDUJW-FQEVSTJZSA-N 0.000 claims 1
- GUETZOYSPCKXKL-UHFFFAOYSA-N 7-[2-(4-fluorophenyl)-2-oxoethoxy]-3-(4-methoxyphenyl)chromen-4-one Chemical compound C1=CC(OC)=CC=C1C1=COC2=CC(OCC(=O)C=3C=CC(F)=CC=3)=CC=C2C1=O GUETZOYSPCKXKL-UHFFFAOYSA-N 0.000 claims 1
- KORFTUYYDNQLIT-UHFFFAOYSA-N 7-[2-[3-(5-bromopyridin-3-yl)-1,2,4-oxadiazol-5-yl]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCC=3ON=C(N=3)C=3C=C(Br)C=NC=3)=CC=C2C1=O KORFTUYYDNQLIT-UHFFFAOYSA-N 0.000 claims 1
- YBMCDYRUWGLIEU-UHFFFAOYSA-N 7-[2-[4-(2-fluorophenyl)piperazin-1-yl]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCN(CC3)C=3C(=CC=CC=3)F)=CC=C2C1=O YBMCDYRUWGLIEU-UHFFFAOYSA-N 0.000 claims 1
- HOPUHQHIURDXAS-UHFFFAOYSA-N 7-[2-[4-(3-fluorophenyl)piperazin-1-yl]ethoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCN(CC3)C=3C=C(F)C=CC=3)=CC=C2C1=O HOPUHQHIURDXAS-UHFFFAOYSA-N 0.000 claims 1
- LVBYYSGNQQWIJS-UHFFFAOYSA-N 7-[3-[(3,5-difluorophenyl)methylamino]-2-hydroxypropoxy]-3-(4-methoxyphenyl)chromen-4-one Chemical compound C1=CC(OC)=CC=C1C1=COC2=CC(OCC(O)CNCC=3C=C(F)C=C(F)C=3)=CC=C2C1=O LVBYYSGNQQWIJS-UHFFFAOYSA-N 0.000 claims 1
- TVYQUGOSXLQOGP-UHFFFAOYSA-N 7-[[3-(3-aminophenyl)-1,2,4-oxadiazol-5-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound NC1=CC=CC(C=2N=C(COC=3C=C4C(C(C(C=5C=CC(O)=CC=5)=CO4)=O)=CC=3)ON=2)=C1 TVYQUGOSXLQOGP-UHFFFAOYSA-N 0.000 claims 1
- IBRIBDVVLALIBW-UHFFFAOYSA-N 7-[[3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]methoxy]-3-[4-[[3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]methoxy]phenyl]chromen-4-one Chemical compound FC(F)(F)C1=CC=CC(C=2N=C(COC=3C=CC(=CC=3)C=3C(C4=CC=C(OCC=5ON=C(N=5)C=5C=C(C=CC=5)C(F)(F)F)C=C4OC=3)=O)ON=2)=C1 IBRIBDVVLALIBW-UHFFFAOYSA-N 0.000 claims 1
- BYZRPKNYQMQCMK-UHFFFAOYSA-N 7-[[3-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3ON=C(N=3)C=3C=C(C=C(F)C=3)C(F)(F)F)=CC=C2C1=O BYZRPKNYQMQCMK-UHFFFAOYSA-N 0.000 claims 1
- WHBOOUQLMQINPB-UHFFFAOYSA-N 7-[[5-(3-chlorophenyl)-1,3,4-oxadiazol-2-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3OC(=NN=3)C=3C=C(Cl)C=CC=3)=CC=C2C1=O WHBOOUQLMQINPB-UHFFFAOYSA-N 0.000 claims 1
- VVVFLKUGSGNQNY-UHFFFAOYSA-N 7-[[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]methoxy]-3-(4-hydroxyphenyl)chromen-4-one Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3OC(=NN=3)C=3C=CC(Cl)=CC=3)=CC=C2C1=O VVVFLKUGSGNQNY-UHFFFAOYSA-N 0.000 claims 1
- WNYYVTUGJCLMLU-UHFFFAOYSA-N 7-[[6-(trifluoromethyl)pyridin-3-yl]methoxy]-3-[4-[[6-(trifluoromethyl)pyridin-3-yl]methoxy]phenyl]chromen-4-one Chemical compound C1=NC(C(F)(F)F)=CC=C1COC1=CC=C(C=2C(C3=CC=C(OCC=4C=NC(=CC=4)C(F)(F)F)C=C3OC=2)=O)C=C1 WNYYVTUGJCLMLU-UHFFFAOYSA-N 0.000 claims 1
- YFTSDZIXAMNCEZ-UHFFFAOYSA-N [3-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]phenyl]boronic acid Chemical compound OB(O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=CC(O)=CC=4)=CO3)=O)=CC=2)=C1 YFTSDZIXAMNCEZ-UHFFFAOYSA-N 0.000 claims 1
- YZSKYZCRDKDSRB-UHFFFAOYSA-N [4-[7-[(3-methoxycarbonylphenyl)methoxy]-4-oxochromen-3-yl]phenyl]boronic acid Chemical compound COC(=O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=CC(=CC=4)B(O)O)=CO3)=O)=CC=2)=C1 YZSKYZCRDKDSRB-UHFFFAOYSA-N 0.000 claims 1
- NDJFEYMUZIFTRQ-UHFFFAOYSA-N [4-[7-[[5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=COC2=CC(OCC=3N=C(ON=3)C=3C=CC(F)=CC=3)=CC=C2C1=O NDJFEYMUZIFTRQ-UHFFFAOYSA-N 0.000 claims 1
- PVGOVCAOHGZDEF-UHFFFAOYSA-N [4-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]phenyl] propanoate Chemical compound C1=CC(OC(=O)CC)=CC=C1COC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 PVGOVCAOHGZDEF-UHFFFAOYSA-N 0.000 claims 1
- VIICMKGBRBRXRG-UHFFFAOYSA-N [4-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1COC1=CC=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 VIICMKGBRBRXRG-UHFFFAOYSA-N 0.000 claims 1
- JSCZRVMYXMJBAJ-UHFFFAOYSA-N methyl 3-[7-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methoxy]-4-oxochromen-3-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2C(C3=CC=C(OCC4=C(N=C(S4)C=4C=CC(=CC=4)C(F)(F)F)C)C=C3OC=2)=O)=C1 JSCZRVMYXMJBAJ-UHFFFAOYSA-N 0.000 claims 1
- FIAYNGLPHFJWNL-UHFFFAOYSA-N methyl 3-[7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2C(C3=CC=C(OCC=4N=C(ON=4)C=4C=C(C=C(F)C=4)C(F)(F)F)C=C3OC=2)=O)=C1 FIAYNGLPHFJWNL-UHFFFAOYSA-N 0.000 claims 1
- LMJMMPUNPQYONN-UHFFFAOYSA-N methyl 3-[[3-(4-acetyloxyphenyl)-4-oxochromen-7-yl]oxymethyl]benzoate Chemical compound COC(=O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=CC(OC(C)=O)=CC=4)=CO3)=O)=CC=2)=C1 LMJMMPUNPQYONN-UHFFFAOYSA-N 0.000 claims 1
- QMLJDJRQXXUTJD-UHFFFAOYSA-N methyl 3-[[3-[4-(2-amino-2-oxoethoxy)phenyl]-4-oxochromen-7-yl]oxymethyl]benzoate Chemical compound COC(=O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=CC(OCC(N)=O)=CC=4)=CO3)=O)=CC=2)=C1 QMLJDJRQXXUTJD-UHFFFAOYSA-N 0.000 claims 1
- KHPANTWQMRVIHT-UHFFFAOYSA-N methyl 3-[[3-[4-(n'-hydroxycarbamimidoyl)phenyl]-4-oxochromen-7-yl]oxymethyl]benzoate Chemical compound COC(=O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=CC(=CC=4)C(N)=NO)=CO3)=O)=CC=2)=C1 KHPANTWQMRVIHT-UHFFFAOYSA-N 0.000 claims 1
- FONJRTAJESCEPB-UHFFFAOYSA-N methyl 3-[[3-[4-[(4-methylphenyl)sulfonylamino]phenyl]-4-oxochromen-7-yl]oxymethyl]benzoate Chemical compound COC(=O)C1=CC=CC(COC=2C=C3C(C(C(C=4C=CC(NS(=O)(=O)C=5C=CC(C)=CC=5)=CC=4)=CO3)=O)=CC=2)=C1 FONJRTAJESCEPB-UHFFFAOYSA-N 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- SZYSQGBOCVSYQS-UHFFFAOYSA-N n-(4-fluorophenyl)-4-[2-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyethyl]piperazine-1-carbothioamide Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCCN3CCN(CC3)C(=S)NC=3C=CC(F)=CC=3)=CC=C2C1=O SZYSQGBOCVSYQS-UHFFFAOYSA-N 0.000 claims 1
- KDHZOCWAWMYCJB-UHFFFAOYSA-N n-[3-[7-[[5-[3-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methoxy]-4-oxochromen-3-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C=2C(C3=CC=C(OCC=4N=C(ON=4)C=4C=C(C=C(F)C=4)C(F)(F)F)C=C3OC=2)=O)=C1 KDHZOCWAWMYCJB-UHFFFAOYSA-N 0.000 claims 1
- IYWMHWZYYBEMLX-UHFFFAOYSA-N n-[4-[4-oxo-7-[[2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl]methoxy]chromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3N=C(SC=3)C=3C=CC(=CC=3)C(F)(F)F)=CC=C2C1=O IYWMHWZYYBEMLX-UHFFFAOYSA-N 0.000 claims 1
- XRXFUBQZEAXFBU-UHFFFAOYSA-N n-[4-[4-oxo-7-[[3-(trifluoromethoxy)phenyl]methoxy]chromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3C=C(OC(F)(F)F)C=CC=3)=CC=C2C1=O XRXFUBQZEAXFBU-UHFFFAOYSA-N 0.000 claims 1
- DYOALZKAPRMVKL-UHFFFAOYSA-N n-[4-[4-oxo-7-[[3-(trifluoromethyl)phenyl]methoxy]chromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(F)(F)F)=CC=C2C1=O DYOALZKAPRMVKL-UHFFFAOYSA-N 0.000 claims 1
- OZIYZNIPBGCGKS-UHFFFAOYSA-N n-[4-[7-[2-[3-[2-fluoro-4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl]ethoxy]-4-oxochromen-3-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCCC=3ON=C(N=3)C=3C(=CC(=CC=3)C(F)(F)F)F)=CC=C2C1=O OZIYZNIPBGCGKS-UHFFFAOYSA-N 0.000 claims 1
- TULOYQLETVYVIG-UHFFFAOYSA-N n-[[4-chloro-3-(trifluoromethyl)phenyl]methyl]-3-[[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxymethyl]benzamide Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(=O)NCC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=C2C1=O TULOYQLETVYVIG-UHFFFAOYSA-N 0.000 claims 1
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- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 238000011870 unpaired t-test Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000001262 western blot Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4245—Oxadiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US98591107P | 2007-11-06 | 2007-11-06 | |
US60/985,911 | 2007-11-06 | ||
PCT/US2008/082643 WO2009061924A2 (en) | 2007-11-06 | 2008-11-06 | Aldh-2 inhibitors in the treatment of psychiatric disorders |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2704981A1 true CA2704981A1 (en) | 2009-05-14 |
Family
ID=40512184
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2704981A Abandoned CA2704981A1 (en) | 2007-11-06 | 2008-11-06 | Aldh-2 inhibitors in the treatment of psychiatric disorders |
Country Status (12)
Country | Link |
---|---|
US (1) | US20090124672A1 (zh) |
EP (1) | EP2231149A2 (zh) |
JP (1) | JP2011503095A (zh) |
KR (1) | KR20100097675A (zh) |
CN (1) | CN101917987A (zh) |
AU (1) | AU2008323953A1 (zh) |
BR (1) | BRPI0820440A2 (zh) |
CA (1) | CA2704981A1 (zh) |
IL (1) | IL205578A0 (zh) |
MX (1) | MX2010005047A (zh) |
RU (1) | RU2010122970A (zh) |
WO (1) | WO2009061924A2 (zh) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8158810B2 (en) * | 2006-07-27 | 2012-04-17 | Gilead Sciences, Inc. | ALDH-2 inhibitors in the treatment of addiction |
US20080207610A1 (en) * | 2006-07-27 | 2008-08-28 | Jeff Zablocki | Aldh-2 inhibitors in the treatment of addiction |
KR20090033417A (ko) * | 2006-07-27 | 2009-04-03 | 씨브이 쎄러퓨틱스, 인코포레이티드 | 중독의 치료에서의 aldh-2 저해제 |
KR20100130589A (ko) * | 2008-01-24 | 2010-12-13 | 질레드 팔로 알토 인코포레이티드 | 중독 치료에서의 aldh-2 저해제 |
CA2713521A1 (en) * | 2008-02-06 | 2009-08-13 | Gilead Palo Alto, Inc. | Use of ranolazine for treating pain |
US8962779B2 (en) | 2013-07-16 | 2015-02-24 | Dow Global Technologies Llc | Method of forming polyaryl polymers |
US9063420B2 (en) | 2013-07-16 | 2015-06-23 | Rohm And Haas Electronic Materials Llc | Photoresist composition, coated substrate, and method of forming electronic device |
US8933239B1 (en) | 2013-07-16 | 2015-01-13 | Dow Global Technologies Llc | Bis(aryl)acetal compounds |
US9410016B2 (en) | 2013-07-16 | 2016-08-09 | Dow Global Technologies Llc | Aromatic polyacetals and articles comprising them |
US20230399299A1 (en) | 2022-06-14 | 2023-12-14 | Amygdala Neurosciences, Inc. | Aldh-2 inhibitor compounds and methods of use |
US12018009B2 (en) | 2022-06-14 | 2024-06-25 | Amygdala Neurosciences, Inc. | ALDH-2 inhibitor compounds and methods of use |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5204369A (en) * | 1991-07-01 | 1993-04-20 | The Endowment For Research In Human Biology | Method for the inhibition of aldh-i useful in the treatment of alcohol dependence or alcohol abuse |
US6255497B1 (en) * | 1997-04-29 | 2001-07-03 | The Endowment For Research In Human Biology, Inc. | Method for the inhibition of ALDH-I useful in the treatment of alcohol dependence or alcohol abuse |
WO1999058124A1 (en) * | 1998-05-12 | 1999-11-18 | The Endowment For Research In Human Biology, Inc. | Methods and assays useful in the treatment of alcohol dependence or alcohol abuse |
EP1294377B1 (en) * | 2000-06-30 | 2011-10-12 | Abdulla Badawy | Methods and compositions for the treatment of alcoholism and alcohol dependence |
JP4933730B2 (ja) * | 2001-05-04 | 2012-05-16 | パラテック ファーマシューティカルズ インコーポレイテッド | 転写因子調節化合物およびその使用法 |
WO2004002470A1 (en) * | 2002-06-27 | 2004-01-08 | The Endowment For Research In Human Biology, Inc. | Compounds useful for the inhibition of aldh |
US20080207610A1 (en) * | 2006-07-27 | 2008-08-28 | Jeff Zablocki | Aldh-2 inhibitors in the treatment of addiction |
KR20090033417A (ko) * | 2006-07-27 | 2009-04-03 | 씨브이 쎄러퓨틱스, 인코포레이티드 | 중독의 치료에서의 aldh-2 저해제 |
CA2682207A1 (en) * | 2007-04-05 | 2008-10-16 | Cv Therapeutics, Inc. | Quinazolinone derivatives as aldh-2 inhibitors |
-
2008
- 2008-11-06 CN CN2008801235666A patent/CN101917987A/zh active Pending
- 2008-11-06 AU AU2008323953A patent/AU2008323953A1/en not_active Abandoned
- 2008-11-06 CA CA2704981A patent/CA2704981A1/en not_active Abandoned
- 2008-11-06 RU RU2010122970/15A patent/RU2010122970A/ru unknown
- 2008-11-06 MX MX2010005047A patent/MX2010005047A/es not_active Application Discontinuation
- 2008-11-06 EP EP08846844A patent/EP2231149A2/en not_active Withdrawn
- 2008-11-06 WO PCT/US2008/082643 patent/WO2009061924A2/en active Application Filing
- 2008-11-06 KR KR1020107012444A patent/KR20100097675A/ko not_active Application Discontinuation
- 2008-11-06 JP JP2010533244A patent/JP2011503095A/ja not_active Withdrawn
- 2008-11-06 BR BRPI0820440-3A patent/BRPI0820440A2/pt not_active IP Right Cessation
- 2008-11-06 US US12/266,288 patent/US20090124672A1/en not_active Abandoned
-
2010
- 2010-05-06 IL IL205578A patent/IL205578A0/en unknown
Also Published As
Publication number | Publication date |
---|---|
BRPI0820440A2 (pt) | 2015-05-26 |
IL205578A0 (en) | 2010-11-30 |
KR20100097675A (ko) | 2010-09-03 |
AU2008323953A1 (en) | 2009-05-14 |
MX2010005047A (es) | 2010-07-28 |
US20090124672A1 (en) | 2009-05-14 |
EP2231149A2 (en) | 2010-09-29 |
RU2010122970A (ru) | 2011-12-20 |
CN101917987A (zh) | 2010-12-15 |
WO2009061924A2 (en) | 2009-05-14 |
WO2009061924A3 (en) | 2009-07-09 |
JP2011503095A (ja) | 2011-01-27 |
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EEER | Examination request | ||
FZDE | Discontinued | ||
FZDE | Discontinued |
Effective date: 20121106 |